HCID 10362064、化合物 → HCID 19026196、化合物

HRID 1586984ノート

反応式

HRID 1586984 の反応式
[CH3:1][Li].[C:3]1([CH2:9][O:10][NH:11][C:12]2([CH3:30])[CH2:21][CH2:20][CH2:19][C:18]3[N:17]=[C:16]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:15]=[CH:14][C:13]2=3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCCC1>[C:3]1([CH2:9][O:10][N:11]([CH3:1])[C:12]2([CH3:30])[CH2:21][CH2:20][CH2:19][C:18]3[N:17]=[C:16]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:15]=[CH:14][C:13]2=3)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 10362064HCID 10362064、化合物HCID 178418348HCID 178418348、化合物

生成物 1

HCID 19026196HCID 19026196、化合物収率 65%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyllithium (1.4 M in diethyl ether, 37.7 ml) was added dropwise over 20 min to a solution of N,2-bis(phenylmethoxy)-5,6,7,8-tetrahydro-5-methyl-5-quinolinamine (18.1 g) and tetrahydrofuran (20 ml) at -78° C. The mixture was allowed to warm to room temperature over 2 hrs. and was stirred at room temperature for an additional 1 hr. The solution was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, filtered, and the filtrate was concentrated. The residue was purified by high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes) to provide 12.3 g (65%) of product.

後処理

  1. customThe solution was quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes)

出典と根拠

ORDレコード
ord-045305e33bd74dd79227109c97a59aff
出典データセット
uspto-grants-1993_06
特許番号
US05216164

反応ノート

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